An enantioselective total synthesis of the stilbenolignan (-)-aiphanol and the determination of its absolute stereochemistry

Tetrahedron Asymmetry

Volumn 16, Issue 9, 2005, Pages 1645-1654

  Banwell, Martin G ^a   Chand, Satish ^a   Savage, G Paul ^b  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AIPHANOL; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 17844397970     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.02.035     Document Type: Article

References (25)

1. D. Lee, M. Cuendet, J. Schunke Vigo, J.G. Graham, F. Cabieses, H.H.S. Fong, J.M. Pezzuto, and A.D. Kinghorn Org. Lett. 3 2001 2169
2. A. Matter Drug Discov. Today 6 2001 1005
3. R.J. Flower Nat. Rev. Drug Discov. 2 2003 179
4. G.A. Fitzgerald Nat. Rev. Drug Discov. 2 2003 879
5. A. Kuboki, T. Yamamoto, and S. Ohira Chem. Lett. 32 2003 420
6. M.G. Banwell, A. Bezos, S. Chand, G. Dannhardt, W. Kiefer, U. Nowe, C.R. Parish, G.P. Savage, and H. Ulbrich Org. Biomol. Chem. 1 2003 2427
7. A.M. Brinker, and D.S. Seigler Phytochemistry 30 1991 3229
8. N.R. Guz, F.R. Stermitz, J.B. Johnson, T.D. Beeson, S. Willen, J.-F. Hsiang, and K. Lewis J. Med. Chem. 44 2001 261 and references cited therein
9. X.L. Wang, J.P. Feng, X.G. Xie, X.P. Cao, and X.F. Pan Chin. Chem. Lett. 15 2004 1036
10. W. Gu, X. Chen, X. Pan, A.S.C. Chan, and T.-K. Yang Tetrahedron: Asymmetry 11 2000 2801
11. A. Arcoleo, A. Bellino, and P. Venturella Ann. Chim. 47 1957 66
12. B.E. Maryanoff, and A.B. Reitz Chem. Rev. 89 1989 863
13. Toshio, W.; Takatoshi, F.; Setsuya, O.; Seiitsu, M. Jap. Patent JP08113567; Chem. Abstr. 1996, 125, 114592
14. H.C. Kolb, M.S. VanNiewenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483
15. H. Becker, P.T. Ho, H.C. Kolb, S. Loren, P.-O. Norrby, and K.B. Sharpless Tetrahedron Lett. 35 1994 7315
16. H.C. Kolb, P.G. Andersson, and K.B. Sharpless J. Am. Chem. Soc. 116 1994 1278
17. M.P. Moon Pyridinium Hydrobromide Perbromide L.A. Paquette Encyclopedia of Reagents for Organic Synthesis Vol. 6 1995 John Wiley and Sons Chichester 4370 4373
18. Details of the X-ray structure analysis will be published elsewhere
19. O. Mitsunobu Synthesis 1981 1 and references cited therein
20. S.V. Kessar, Y.P. Gupta, T. Mohammad, M. Goyal, and K.K. Sawal J. Chem. Soc., Chem. Commun. 1983 400
21. B. Hegedus Helv. Chim. Acta 1963 2604 The structure of compound 11 has been unequivocally established by X-ray crystallographic means. Details will be reported elsewhere
22. T. Ganesh, and G.L.D. Krupadanam Synth. Commun. 28 1998 3121
23. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923
24. D.D. Perrin, and W.L.F. Armarego Purification of Laboratory Chemicals 3rd ed. 1988 Pergamon Oxford
25. C.A. Townsend, S.G. Davis, S.B. Christensen, J.C. Link, and C.P. Lewis J. Am. Chem. Soc. 103 1981 6885